Central Planning Cycle Scheduler - Part Time

Overview

Copilot ships on a fast, high-visibility rhythm, and the teams building it plan and execute in 12-week Cycles broken into meetups, milestones, and sprints. The Copilot Program Management Office (PMO) is the team that keeps that system running: we own release visibility, drive effective planning across every engineering and product effort, and make sure the trains run on time across a large, cross-organizational group.

We are looking for a Central Planning Cycle Scheduler (Part Time) to own the operational backbone of the Cycle system. This person keeps the planning calendar, drives the cadence of reviews and checkpoints, safeguards the integrity of our planning data, and communicates relentlessly so that dozens of work streams and squads know exactly what is due, when, and where the risks are.

You will be the connective tissue between leadership reviews and the day-to-day execution of teams, turning a complex, multi-team planning model into a predictable, repeatable operation.

This is a senior individual-contributor role with broad reach. You will coordinate across product, engineering, design, finance, and partner organizations, and you will influence far more people than you direct. Success looks like planning that starts on time, milestones that are visible before they slip, and a Cycle rhythm that leaders and builders alike can trust. If you take pride in bringing order to ambiguity and enjoy being the person who always knows the plan, this role is for you.

• Build and maintain the master planning calendar for the 12-week Cycle, including the meetup and kickoff week, execution sprints, the midpoint replanning checkpoint, demos, retrospectives, and end-of-cycle reviews.

• Schedule and coordinate the recurring leadership cadence: leadership reviews, monthly business reviews, and the Cycle's leadership checkpoints, and ensure the workstream-level review calendar aligns to it.

• Run the planning timeline for the next Cycle in parallel with the current one, since next-cycle planning begins at mid-cycle. Sequence proposal drafts, leadership alignment sessions, mission-sheet reviews, and finalization of work streams, DRIs, and squads ahead of the next meetup.

• Track milestones, sprint progress, and status across all work streams; maintain a launch and release view so teams have a single, current picture of major launches, cross-team dependencies, and readiness blockers.

• Monitor progress against plan, surface delays, resource conflicts, and schedule slips early, and drive the follow-ups that keep commitments on track.

• Facilitate the midpoint replan: help workstream owners decide where course corrections are needed and reflect those changes cleanly in the plan.

• Own the structure and readiness standards of the team's system of record: define what a complete, execution-ready plan looks like each Cycle and the checkpoints where readiness is verified.

• Drive mission-sheet readiness each Cycle so that every workstream and squad enters execution with clear, measurable outcomes.

• Manage change: keep the plan current as scope, priorities, resourcing, and dependencies shift, with minimal disruption to teams.

• Serve as the central point of coordination for planning and execution across product, engineering, design, finance, and partner organizations.

• Manage cross-workstream dependencies, shared squads, and resource contention; help identify counterpart owners and align ownership across partner organizations.

• Communicate clearly and proactively to a large audience: publish schedules and deadlines, send timely reminders ahead of checkpoints, and make sure every team knows what is expected and by when.

• Turn planning knowledge that lives in people's heads into repeatable, documented processes, templates, and governance.

• Continuously improve the planning operation through process refinement, better tooling, and automation, including AI-assisted planning, forecasting, and reporting where it adds accuracy and saves time.

Required / Minimum Qualifications

• Bachelor's Degree in relevant field (e.g., Liberal Arts, Business Administration, Management, Computer Science) AND 4+ years experience in financial management, business planning, operations management, strategy, project management, human resources, or business-related roles OR equivalent experience.

Additional / Preferred Qualifications

• Demonstrated experience owning schedules, calendars, and delivery cadence for large, cross-functional programs.
• Proficiency with project and program planning tools such as Microsoft Project, Smartsheet, Jira, Azure Dev Ops, or comparable platforms.
• Excellent written and verbal communication and the ability to keep a large, distributed group aligned and informed.
• Experience supporting a Program Management Office or a…